Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron
| Autor: | Dinith R. Jayanetti, Geoffrey Bartholomeusz, Gerald F. Bills, Yan Li, Qun Yue, James B. Gloer, Zhiqiang An, Dale C. Swenson |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Antifungal Agents Stereochemistry Cryptococcus Pharmaceutical Science Breast Neoplasms Microbial Sensitivity Tests Crystallography X-Ray Ring (chemistry) Peptides Cyclic 01 natural sciences Article Hydrolysate Analytical Chemistry 03 medical and health sciences Ascomycota Candida albicans Drug Discovery Humans Molecule Nuclear Magnetic Resonance Biomolecular Pharmacology Cryptococcus neoformans Molecular Structure biology 010405 organic chemistry Chemistry Organic Chemistry Diastereomer Phenalenes biology.organism_classification 0104 chemical sciences Solvent 030104 developmental biology Complementary and alternative medicine Molecular Medicine Female |
| Zdroj: | Journal of Natural Products. 80:2101-2109 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.7b00341 |
| Popis: | Auxarthrones A–E (1–5), five new phenalenones, and two new naturally occurring cyclic tetrapeptides, auxarthrides A (7) and B (8), were obtained from three different solvent extracts of cultures of the coprophilous fungus Auxarthron pseudauxarthron. Auxarthrones C (3) and E (5) possess an unusual 7a,8-dihydrocyclopenta[a]phenalene-7,9-dione ring system that has not been previously observed in natural products. Formation of 1–5 was found to be dependent on the solvent used for culture extraction. The structures of these new compounds were elucidated primarily by analysis of NMR and MS data. Auxarthrone A (1) was obtained as a mixture of chromatographically inseparable racemic diastereomers (1a and 1b) that cocrystallized, enabling confirmation of their structures by X-ray crystallography. The absolute configurations of 7 and 8 were assigned by analysis of their acid hydrolysates using Marfey’s method. Compound 1 displayed moderate antifungal activity against Cryptococcus neoformans and Candida albicans, but did not affect human cancer cell lines. |
| Databáze: | OpenAIRE |
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